A kind of method taking androstenedione as raw material to synthesize lithocholic acid
A technology of androstenedione and lithocholic acid, applied in the direction of steroids, organic chemistry, etc., can solve the problems of difficult operation, danger, workshop implementation, etc., achieve low cost, solve difficult large-scale production, and simple process route Effect
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Embodiment 1
[0050] Preparation of compound (A) 3-methoxy-3,5-dienandrost-17-one:
[0051] Add 20g of 4-androstenedione to the reaction kettle, add 80ml of anhydrous THF, 14ml of methanol and 0.24g of anhydrous p-toluenesulfonic acid, add 20.1g of trimethyl orthoacetate under nitrogen protection, and heat up to 30°C. The reaction was incubated for 4 hours, and the reaction was tracked by TLC. After the reaction was completed, triethylamine was added to adjust the pH of the reaction system to 8~10. Concentrate under reduced pressure, wash with a small amount of methanol, filter with suction, and pass the filtrate through a column to obtain a light yellow substance, which is dried in vacuo at 40°C to obtain 19.7g of the product with a molar yield of 94%.
Embodiment 2
[0053] Preparation of compound (B) 3-methoxy-17(Z)-pregna-3(4),5(6),17(20)-triene:
[0054] The product compound (A) obtained in Example 1 was used as a raw material; 18g of ethyltriphenylphosphine bromide was added to the reaction kettle, 144ml of anhydrous THF was added, and 8g of potassium tert-butoxide was added in batches at low temperature under the protection of nitrogen. Do not exceed 0°C. At this time, the solution is an orange-red to blood-red suspension. React at low temperature for 1 hour, add 4.2 g of compound (A) 3-methoxy-3,5-dienandrost-17-one, and continue the low-temperature reaction After 0.5h, it was transferred to 50°C for 6h, quenched with cold water, extracted with petroleum ether and concentrated to an oily substance at 35°C, and the target compound was precipitated with methanol. After filtration, 40.5 kg of high-purity compound B 3-methoxy-17(Z)-pregna-3(4),5(6),17(20)-triene was obtained, with a molar yield of 92.7%.
Embodiment 3
[0056] Compound (C) Preparation of 17(Z)-pregna-4,17(20)-dien-3-one:
[0057]Using the product compound (B) obtained in Example 2 as a raw material; compound B 3-methoxy-17(Z)-pregna-3(4),5(6),17(20)-triene 4.05g, Dissolve in 20ml of THF, add 4.8ml of 30% dilute hydrochloric acid dropwise for deprotection, after the reaction is completed, dilute with ethyl acetate, wash twice with 10% sodium bicarbonate, wash with saturated saline, dry over anhydrous sodium sulfate, and concentrate under reduced pressure to obtain The yellow oily substance was precipitated by adding cold methanol, filtered to obtain 3.76 g of high-purity compound C 17(Z)-pregna-4,17(20)-dien-3-one, and the filtrate was passed through the column with PE:EA=5:1. Compound C was vacuum-dried at 40°C, and the molar yield was 97%.
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